The present invention relates to a process for producing N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1-trifluoromethanesulfonamide represented by formula [3], which is a useful compound as an organic intermediate, such as monomers corresponding to the next generation photoresist.

N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1-trifluoromethanesulfonamide represented by formula [3] is a useful compound as an organic intermediate, the useful compound being expected to be, for example, a monomer corresponding to the next generation photoresist.
It is disclosed in non-patent publication 1 that N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1-trifluoromethanesulfonamide can be synthesized by the following process “a” or process “b”.
[Process “a”]
It is a process in which trifluoromethanesulfonic anhydride represented by formula [1] is reacted with 1-bicyclo[2.2.1]hept-5-en-2-ylmethaneamine represented by formula [2] in an anhydrous methylene chloride solvent in the presence of triethylamine serving as a base.(CF3SO2)2O   [1]
[Process “b”]
It is a process in which trifluoromethanesulfonic fluoride represented by formula [4] is reacted with 1-bicyclo[2.2.1]hept-5-en-2-ylmethaneamine represented by formula [2] in an anhydrous methylene chloride solvent in the presence of triethylamine serving as a base.CF3SO2F   [4]
A sulfonamidation reaction in which a sulfonic halide is used as a sulfonation agent is a well-known process in general. With this reaction, a sulfonamide compound can be produced with relatively high selectivity. Other than the above-mentioned process “b” in which trifluoromethanesulfonic fluoride is used as a raw material, there is known an example as follows, though the target compound thereof is different from that of process “b”.
(Example of Non-Patent Publication 2)
Trifluoromethanesulfonic chloride represented by formula [5] is used as a sulfonation agent. This is reacted with aniline in an anhydrous ether solvent in the presence of pyridine serving as a base, thereby synthesizing trifluoromethanesulfonic anilide.CF3SO2Cl   [5](Example of Non-Patent Publication 1)
As a sulfonation agent, m-trifluoromethylphenylsulfonic chloride is used. This is reacted with 1-bicyclo[2.2.1]hept-5-en-2-ylmethaneamine represented by formula [2] in an ether solvent in the presence of 20% sodium hydroxide aqueous solution serving as a base, thereby synthesizing N-(m-trifluoromethylphenylsulfonyl)-5-aminomethylbicyclo[2.2.1]hept-2-en. In addition to this, patent publications 1 to 3, etc. are known as reaction examples of forming a [—SO2—NH—] bond by reacting a sulfonic halide containing a trifluoromethyl group with an amine-series compound.
[Non-patent Publication 1] Zhurnal OrganicheskoiKhimii (Russia), (1995), 31 (3), p. 357-64
[Non-patent Publication 2] Journal of Chemical Society, vol. 6 (5), p. 2574-2578 (published in 1957)
[Patent Publication 1] Japanese Patent Application Publication 8-81436
[Patent Publication 2] Japanese Patent Application Publication 11-209338
[Patent Publication 3] International Publication 97/23448 Pamphlet